3,3,6,6-Tetra­methyl-9-(3,4-methyl­ene­dioxyl­phenyl)-1,2,3,4,5,6,7,8,9,10-deca­hydro­acridine-1,8-dione

The crystal structure of the title compound, C₂₄H₂₇NO₄, reveals that there are two roughly identical mol­ecules in the asymmetric unit. In both acridine moieties, the central pyridine rings are slightly distorted and adopt a boat conformation, whereas the two outer six-membered rings display half-chair conformations. Each mol­ecule is linked through N—H...O hydrogen bonds to symmetry-related mol­ecules, forming infinite chains.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.040
• wR factor = 0.090
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....         O4
PLAT241_ALERT_2_B Check High   U(eq) as Compared to Neighbors ....         O8

Alert level C
GOODF01_ALERT_2_C  The least squares goodness of fit parameter lies
            outside the range 0.80 <> 2.00
            Goodness of fit given =      0.748
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         40 Perc.
PLAT242_ALERT_2_C Check Low    U(eq) as Compared to Neighbors ....        C35
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      38.00 A   3  

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           27.00
           From the CIF: _reflns_number_total               4854
           Count of symmetry unique reflns         4854
           Completeness (_total/calc)            100.00%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present           no

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

3,3,6,6-tetramethyl-9-(3,4-methylenedioxylphenyl)- 1,2,3,4,5,6,7,8,9,10-decahydroacridines-1,8-dione

Crystal data

C24H27NO4	Dx = 1.210 Mg m^−3
Mr = 393.47	Melting point: 600 K
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 27 reflections
a = 14.080 (2) Å	θ = 3.1–12.0°
b = 15.158 (3) Å	µ = 0.08 mm^−1
c = 20.233 (4) Å	T = 296 K
V = 4318.1 (14) Å^3	Block, yellow
Z = 8	0.58 × 0.36 × 0.12 mm
F(000) = 1680

Data collection

Siemens P4 diffractometer	Rint = 0.031
Radiation source: normal-focus sealed tube	θmax = 27.0°, θmin = 1.3°
Graphite monochromator	h = 0→17
ω scans	k = 0→19
8775 measured reflections	l = −21→25
4854 independent reflections	3 standard reflections every 97 reflections
1942 reflections with I > 2σ(I)	intensity decay: 7.4%

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.090	H-atom parameters constrained
S = 0.75	w = 1/[σ^2(Fo^2) + (0.0355P)^2] where P = (Fo^2 + 2Fc^2)/3
4854 reflections	(Δ/σ)max < 0.001
531 parameters	Δρmax = 0.18 e Å^−3
67 restraints	Δρmin = −0.16 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.4793 (2)	0.2161 (2)	0.44293 (19)	0.0736 (11)
O2	0.33067 (19)	0.4685 (2)	0.57109 (19)	0.0598 (10)
O3	0.3241 (3)	0.5267 (3)	0.2536 (2)	0.0708 (11)
O4	0.2272 (2)	0.4378 (3)	0.3172 (2)	0.0994 (14)
N1	0.6570 (2)	0.4546 (2)	0.52459 (19)	0.0431 (10)
H1	0.7111	0.4808	0.5268	0.052*
C1	0.6500 (3)	0.3748 (3)	0.4906 (2)	0.0400 (11)
C2	0.7422 (3)	0.3323 (3)	0.4734 (2)	0.0502 (13)
H2A	0.7691	0.3060	0.5129	0.060*
H2B	0.7860	0.3773	0.4580	0.060*
C3	0.7324 (3)	0.2609 (3)	0.4198 (2)	0.0503 (13)
C4	0.6481 (3)	0.2036 (3)	0.4379 (3)	0.0550 (14)
H4A	0.6370	0.1624	0.4020	0.066*
H4B	0.6647	0.1692	0.4767	0.066*
C5	0.5570 (3)	0.2518 (3)	0.4519 (2)	0.0498 (13)
C6	0.5638 (3)	0.3400 (3)	0.4786 (2)	0.0377 (11)
C7	0.4738 (3)	0.3920 (3)	0.4911 (2)	0.0431 (12)
H7	0.4261	0.3511	0.5086	0.052*
C8	0.4924 (3)	0.4616 (3)	0.5437 (2)	0.0355 (11)
C9	0.4127 (3)	0.4955 (3)	0.5813 (3)	0.0425 (14)
C10	0.4331 (3)	0.5600 (3)	0.6346 (2)	0.0523 (13)
H10A	0.4474	0.5280	0.6749	0.063*
H10B	0.3765	0.5950	0.6426	0.063*
C11	0.5152 (3)	0.6218 (3)	0.6193 (2)	0.0481 (13)
C12	0.6019 (3)	0.5658 (3)	0.6022 (2)	0.0467 (12)
H12A	0.6503	0.6034	0.5830	0.056*
H12B	0.6275	0.5406	0.6425	0.056*
C13	0.5794 (3)	0.4926 (3)	0.5547 (3)	0.0369 (13)
C14	0.4343 (3)	0.4316 (3)	0.4275 (2)	0.0445 (12)
C15	0.4914 (4)	0.4881 (3)	0.3900 (3)	0.0607 (17)
H15	0.5517	0.5030	0.4052	0.073*
C16	0.4592 (4)	0.5224 (4)	0.3299 (3)	0.0659 (17)
H16	0.4976	0.5584	0.3040	0.079*
C17	0.3701 (4)	0.5013 (3)	0.3109 (3)	0.0504 (15)
C18	0.3138 (3)	0.4497 (3)	0.3477 (3)	0.0559 (14)
C19	0.3430 (3)	0.4130 (3)	0.4066 (3)	0.0571 (14)
H19	0.3029	0.3770	0.4313	0.069*
C20	0.2341 (5)	0.4888 (4)	0.2581 (3)	0.081 (2)
H20A	0.2229	0.4514	0.2200	0.097*
H20B	0.1862	0.5348	0.2583	0.097*
C21	0.8233 (3)	0.2053 (3)	0.4181 (3)	0.0738 (16)
H21A	0.8321	0.1772	0.4602	0.111*
H21B	0.8767	0.2428	0.4089	0.111*
H21C	0.8180	0.1613	0.3842	0.111*
C22	0.7149 (4)	0.3041 (3)	0.3522 (3)	0.0762 (17)
H22A	0.7022	0.2592	0.3199	0.114*
H22B	0.7702	0.3370	0.3393	0.114*
H22C	0.6614	0.3432	0.3552	0.114*
C23	0.5382 (3)	0.6786 (3)	0.6812 (3)	0.0706 (16)
H23A	0.4831	0.7121	0.6935	0.106*
H23B	0.5896	0.7180	0.6712	0.106*
H23C	0.5561	0.6406	0.7171	0.106*
C24	0.4876 (3)	0.6818 (3)	0.5619 (2)	0.0593 (14)
H24A	0.4765	0.6467	0.5232	0.089*
H24B	0.5380	0.7228	0.5534	0.089*
H24C	0.4308	0.7135	0.5731	0.089*
O5	0.0994 (2)	0.9777 (2)	0.0301 (2)	0.0590 (10)
O6	0.2455 (2)	0.7192 (2)	0.1562 (2)	0.0722 (10)
O7	0.0666 (3)	1.0093 (3)	0.3454 (2)	0.0852 (14)
O8	−0.0227 (3)	0.9229 (3)	0.2744 (2)	0.1050 (15)
N2	0.4239 (2)	0.9612 (2)	0.08287 (18)	0.0437 (10)
H2	0.4780	0.9875	0.0825	0.052*
C25	0.3478 (3)	1.0003 (3)	0.0527 (3)	0.0359 (13)
C26	0.3717 (3)	1.0765 (3)	0.0078 (2)	0.0444 (12)
H26A	0.3995	1.0536	−0.0325	0.053*
H26B	0.4191	1.1131	0.0293	0.053*
C27	0.2859 (3)	1.1337 (3)	−0.0100 (2)	0.0489 (12)
C28	0.2049 (3)	1.0716 (3)	−0.0289 (2)	0.0545 (13)
H28A	0.1485	1.1065	−0.0375	0.065*
H28B	0.2217	1.0416	−0.0696	0.065*
C29	0.1819 (3)	1.0041 (3)	0.0225 (3)	0.0455 (15)
C30	0.2599 (3)	0.9688 (3)	0.0612 (2)	0.0362 (11)
C31	0.2390 (3)	0.8954 (3)	0.1097 (2)	0.0407 (11)
H31	0.1939	0.8546	0.0889	0.049*
C32	0.3298 (3)	0.8451 (3)	0.1242 (2)	0.0402 (12)
C33	0.3226 (3)	0.7555 (3)	0.1503 (3)	0.0477 (12)
C34	0.4127 (3)	0.7069 (3)	0.1662 (3)	0.0561 (15)
H34A	0.4316	0.6728	0.1279	0.067*
H34B	0.4002	0.6657	0.2019	0.067*
C35	0.4948 (3)	0.7665 (3)	0.1863 (2)	0.0438 (12)
C36	0.5077 (3)	0.8371 (3)	0.1323 (2)	0.0473 (12)
H36A	0.5518	0.8816	0.1480	0.057*
H36B	0.5351	0.8099	0.0934	0.057*
C37	0.4158 (3)	0.8806 (3)	0.1138 (2)	0.0384 (11)
C38	0.1940 (3)	0.9301 (3)	0.1736 (2)	0.0432 (12)
C39	0.2447 (4)	0.9844 (4)	0.2154 (3)	0.0623 (17)
H39	0.3059	1.0014	0.2037	0.075*
C40	0.2067 (4)	1.0144 (4)	0.2744 (3)	0.0713 (18)
H40	0.2411	1.0513	0.3022	0.086*
C41	0.1183 (4)	0.9884 (4)	0.2900 (3)	0.0573 (16)
C42	0.0665 (3)	0.9365 (3)	0.2489 (3)	0.0566 (13)
C43	0.1022 (3)	0.9070 (3)	0.1897 (3)	0.0527 (13)
H43	0.0656	0.8727	0.1614	0.063*
C44	−0.0221 (4)	0.9649 (5)	0.3375 (3)	0.088 (2)
H44A	−0.0303	0.9214	0.3721	0.106*
H44B	−0.0739	1.0069	0.3403	0.106*
C45	0.3115 (4)	1.1947 (3)	−0.0677 (3)	0.0736 (18)
H45A	0.3311	1.1599	−0.1049	0.110*
H45B	0.3624	1.2331	−0.0548	0.110*
H45C	0.2570	1.2294	−0.0796	0.110*
C46	0.2543 (3)	1.1896 (3)	0.0494 (3)	0.0691 (17)
H46A	0.2019	1.2264	0.0367	0.104*
H46B	0.3062	1.2260	0.0638	0.104*
H46C	0.2352	1.1515	0.0848	0.104*
C47	0.5879 (3)	0.7133 (3)	0.1917 (3)	0.0705 (16)
H47A	0.5815	0.6695	0.2257	0.106*
H47B	0.6393	0.7524	0.2025	0.106*
H47C	0.6008	0.6849	0.1503	0.106*
C48	0.4752 (3)	0.8089 (3)	0.2534 (3)	0.0686 (15)
H48A	0.4189	0.8444	0.2506	0.103*
H48B	0.5280	0.8453	0.2658	0.103*
H48C	0.4663	0.7635	0.2860	0.103*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.066 (2)	0.058 (2)	0.097 (3)	−0.021 (2)	0.002 (2)	−0.013 (2)
O2	0.0337 (18)	0.0568 (19)	0.089 (3)	0.0013 (16)	0.0045 (19)	0.018 (2)
O3	0.075 (3)	0.085 (2)	0.052 (3)	0.002 (2)	−0.019 (2)	0.014 (2)
O4	0.066 (3)	0.137 (4)	0.095 (3)	−0.030 (2)	−0.041 (2)	0.041 (3)
N1	0.0253 (19)	0.045 (2)	0.058 (3)	−0.0020 (17)	0.003 (2)	−0.001 (2)
C1	0.043 (3)	0.037 (3)	0.040 (3)	0.001 (2)	−0.004 (2)	−0.002 (2)
C2	0.041 (3)	0.047 (3)	0.063 (4)	0.005 (2)	0.007 (3)	−0.004 (3)
C3	0.050 (3)	0.050 (3)	0.051 (3)	0.003 (3)	0.005 (3)	0.002 (3)
C4	0.069 (3)	0.041 (3)	0.055 (4)	0.009 (3)	0.003 (3)	0.000 (3)
C5	0.055 (3)	0.051 (3)	0.044 (3)	−0.009 (3)	0.004 (3)	0.005 (3)
C6	0.036 (2)	0.039 (3)	0.038 (3)	−0.003 (2)	−0.003 (2)	0.001 (2)
C7	0.035 (2)	0.042 (3)	0.052 (3)	−0.010 (2)	−0.007 (2)	0.013 (3)
C8	0.024 (2)	0.038 (2)	0.045 (3)	−0.0012 (19)	−0.002 (2)	0.006 (3)
C9	0.036 (3)	0.037 (3)	0.054 (4)	0.005 (2)	0.002 (3)	0.013 (2)
C10	0.046 (3)	0.046 (3)	0.065 (3)	0.012 (2)	0.014 (3)	0.010 (3)
C11	0.041 (3)	0.047 (3)	0.057 (3)	0.009 (2)	−0.002 (2)	0.003 (3)
C12	0.044 (3)	0.049 (3)	0.048 (3)	0.004 (2)	−0.001 (2)	0.001 (2)
C13	0.034 (3)	0.036 (3)	0.041 (3)	0.003 (2)	0.007 (2)	0.003 (2)
C14	0.038 (3)	0.043 (3)	0.052 (3)	−0.001 (2)	−0.005 (2)	0.002 (2)
C15	0.052 (3)	0.072 (4)	0.058 (4)	−0.018 (3)	−0.014 (3)	0.026 (3)
C16	0.072 (4)	0.074 (4)	0.052 (4)	−0.024 (3)	−0.005 (3)	0.022 (3)
C17	0.055 (3)	0.051 (3)	0.045 (4)	0.000 (3)	−0.014 (3)	0.007 (3)
C18	0.044 (3)	0.063 (3)	0.061 (4)	−0.006 (3)	−0.014 (3)	−0.001 (3)
C19	0.046 (3)	0.060 (3)	0.065 (4)	−0.006 (3)	−0.015 (3)	0.014 (3)
C20	0.088 (5)	0.099 (5)	0.056 (4)	0.015 (4)	−0.035 (4)	0.005 (4)
C21	0.080 (4)	0.062 (4)	0.079 (4)	0.017 (3)	0.019 (3)	−0.009 (3)
C22	0.099 (4)	0.077 (4)	0.052 (4)	−0.003 (3)	0.005 (3)	0.012 (3)
C23	0.072 (4)	0.061 (3)	0.078 (4)	0.008 (3)	0.003 (3)	−0.025 (3)
C24	0.053 (3)	0.052 (3)	0.073 (4)	0.004 (2)	−0.007 (3)	0.015 (3)
O5	0.0335 (18)	0.069 (2)	0.074 (3)	−0.0031 (16)	−0.0019 (19)	−0.015 (2)
O6	0.066 (2)	0.054 (2)	0.097 (3)	−0.0249 (19)	0.001 (2)	0.011 (2)
O7	0.087 (3)	0.115 (4)	0.053 (3)	0.016 (3)	0.032 (3)	0.003 (2)
O8	0.081 (3)	0.135 (4)	0.098 (3)	−0.024 (3)	0.054 (3)	−0.018 (3)
N2	0.034 (2)	0.040 (2)	0.057 (3)	−0.0079 (17)	−0.0065 (19)	0.015 (2)
C25	0.027 (2)	0.042 (3)	0.038 (3)	0.003 (2)	0.000 (2)	0.000 (2)
C26	0.040 (2)	0.045 (3)	0.048 (3)	0.006 (2)	0.001 (2)	0.003 (2)
C27	0.048 (3)	0.042 (3)	0.057 (3)	0.010 (2)	−0.003 (3)	0.004 (3)
C28	0.045 (3)	0.056 (3)	0.062 (3)	0.011 (2)	−0.014 (3)	0.001 (3)
C29	0.039 (3)	0.047 (3)	0.051 (4)	0.002 (2)	0.001 (3)	−0.014 (3)
C30	0.029 (2)	0.042 (2)	0.037 (3)	0.005 (2)	0.001 (2)	−0.008 (3)
C31	0.028 (2)	0.045 (3)	0.049 (3)	−0.003 (2)	0.004 (2)	−0.012 (2)
C32	0.039 (3)	0.036 (3)	0.046 (3)	−0.003 (2)	0.009 (2)	−0.004 (2)
C33	0.054 (3)	0.042 (3)	0.047 (3)	−0.011 (3)	0.005 (3)	−0.007 (3)
C34	0.067 (3)	0.041 (3)	0.060 (4)	−0.001 (3)	0.005 (3)	0.002 (3)
C35	0.052 (3)	0.040 (2)	0.039 (3)	0.003 (2)	0.000 (2)	−0.002 (2)
C36	0.044 (3)	0.047 (3)	0.052 (3)	0.002 (2)	0.005 (2)	0.002 (3)
C37	0.034 (2)	0.042 (3)	0.039 (3)	0.004 (2)	−0.002 (2)	0.000 (2)
C38	0.036 (2)	0.050 (3)	0.044 (3)	0.000 (2)	0.007 (2)	0.000 (2)
C39	0.041 (3)	0.087 (4)	0.059 (4)	−0.010 (3)	0.014 (3)	−0.019 (3)
C40	0.061 (4)	0.100 (5)	0.053 (4)	0.000 (3)	−0.004 (3)	−0.031 (4)
C41	0.055 (3)	0.078 (4)	0.038 (4)	0.013 (3)	0.010 (3)	0.008 (3)
C42	0.047 (3)	0.060 (3)	0.063 (4)	−0.002 (3)	0.022 (3)	0.008 (3)
C43	0.045 (3)	0.053 (3)	0.060 (3)	−0.007 (3)	0.007 (3)	−0.005 (3)
C44	0.078 (4)	0.119 (5)	0.069 (5)	0.013 (4)	0.039 (4)	0.032 (4)
C45	0.084 (4)	0.062 (4)	0.075 (4)	0.017 (3)	−0.004 (4)	0.016 (3)
C46	0.060 (3)	0.051 (3)	0.096 (5)	0.003 (3)	0.005 (3)	−0.022 (3)
C47	0.075 (4)	0.063 (3)	0.073 (4)	0.016 (3)	−0.010 (3)	0.018 (3)
C48	0.083 (4)	0.074 (3)	0.050 (4)	0.003 (3)	−0.001 (3)	−0.003 (3)

Geometric parameters (Å, º)

O1—C5	1.234 (5)	O5—C29	1.239 (5)
O2—C9	1.243 (5)	O6—C33	1.222 (5)
O3—C17	1.382 (7)	O7—C41	1.373 (7)
O3—C20	1.394 (7)	O7—C44	1.428 (6)
O4—C18	1.378 (5)	O8—C42	1.373 (5)
O4—C20	1.429 (7)	O8—C44	1.426 (7)
N1—C13	1.376 (5)	N2—C25	1.369 (5)
N1—C1	1.396 (5)	N2—C37	1.377 (5)
N1—H1	0.8600	N2—H2	0.8600
C1—C6	1.346 (5)	C25—C30	1.336 (5)
C1—C2	1.490 (5)	C25—C26	1.507 (6)
C2—C3	1.538 (6)	C26—C27	1.531 (5)
C2—H2A	0.9700	C26—H26A	0.9700
C2—H2B	0.9700	C26—H26B	0.9700
C3—C4	1.516 (5)	C27—C28	1.528 (5)
C3—C21	1.533 (6)	C27—C45	1.533 (7)
C3—C22	1.536 (6)	C27—C46	1.536 (6)
C4—C5	1.503 (6)	C28—C29	1.495 (7)
C4—H4A	0.9700	C28—H28A	0.9700
C4—H4B	0.9700	C28—H28B	0.9700
C5—C6	1.446 (6)	C29—C30	1.451 (6)
C6—C7	1.514 (5)	C30—C31	1.514 (6)
C7—C8	1.521 (6)	C31—C32	1.518 (5)
C7—C14	1.526 (6)	C31—C38	1.533 (6)
C7—H7	0.9800	C31—H31	0.9800
C8—C13	1.331 (5)	C32—C37	1.343 (5)
C8—C9	1.450 (6)	C32—C33	1.460 (6)
C9—C10	1.485 (7)	C33—C34	1.503 (6)
C10—C11	1.520 (5)	C34—C35	1.523 (6)
C10—H10A	0.9700	C34—H34A	0.9700
C10—H10B	0.9700	C34—H34B	0.9700
C11—C24	1.524 (6)	C35—C48	1.527 (6)
C11—C12	1.526 (5)	C35—C36	1.539 (6)
C11—C23	1.553 (6)	C35—C47	1.543 (6)
C12—C13	1.501 (6)	C36—C37	1.500 (5)
C12—H12A	0.9700	C36—H36A	0.9700
C12—H12B	0.9700	C36—H36B	0.9700
C14—C19	1.382 (6)	C38—C43	1.379 (5)
C14—C15	1.399 (6)	C38—C39	1.380 (7)
C15—C16	1.397 (8)	C39—C40	1.385 (8)
C15—H15	0.9300	C39—H39	0.9300
C16—C17	1.351 (7)	C40—C41	1.343 (8)
C16—H16	0.9300	C40—H40	0.9300
C17—C18	1.340 (7)	C41—C42	1.359 (7)
C18—C19	1.378 (6)	C42—C43	1.373 (6)
C19—H19	0.9300	C43—H43	0.9300
C20—H20A	0.9700	C44—H44A	0.9700
C20—H20B	0.9700	C44—H44B	0.9700
C21—H21A	0.9600	C45—H45A	0.9600
C21—H21B	0.9600	C45—H45B	0.9600
C21—H21C	0.9600	C45—H45C	0.9600
C22—H22A	0.9600	C46—H46A	0.9600
C22—H22B	0.9600	C46—H46B	0.9600
C22—H22C	0.9600	C46—H46C	0.9600
C23—H23A	0.9600	C47—H47A	0.9600
C23—H23B	0.9600	C47—H47B	0.9600
C23—H23C	0.9600	C47—H47C	0.9600
C24—H24A	0.9600	C48—H48A	0.9600
C24—H24B	0.9600	C48—H48B	0.9600
C24—H24C	0.9600	C48—H48C	0.9600
C17—O3—C20	104.9 (5)	C41—O7—C44	105.3 (5)
C18—O4—C20	104.1 (4)	C42—O8—C44	105.4 (5)
C13—N1—C1	121.7 (3)	C25—N2—C37	121.5 (3)
C13—N1—H1	119.2	C25—N2—H2	119.3
C1—N1—H1	119.2	C37—N2—H2	119.3
C6—C1—N1	119.5 (4)	C30—C25—N2	120.9 (4)
C6—C1—C2	125.1 (4)	C30—C25—C26	123.9 (4)
N1—C1—C2	115.4 (4)	N2—C25—C26	115.2 (3)
C1—C2—C3	113.0 (4)	C25—C26—C27	113.6 (3)
C1—C2—H2A	109.0	C25—C26—H26A	108.9
C3—C2—H2A	109.0	C27—C26—H26A	108.9
C1—C2—H2B	109.0	C25—C26—H26B	108.9
C3—C2—H2B	109.0	C27—C26—H26B	108.9
H2A—C2—H2B	107.8	H26A—C26—H26B	107.7
C4—C3—C21	110.1 (4)	C28—C27—C26	107.4 (3)
C4—C3—C22	109.5 (4)	C28—C27—C45	110.8 (4)
C21—C3—C22	110.4 (4)	C26—C27—C45	109.6 (4)
C4—C3—C2	107.7 (4)	C28—C27—C46	108.7 (4)
C21—C3—C2	109.1 (4)	C26—C27—C46	111.0 (4)
C22—C3—C2	110.0 (4)	C45—C27—C46	109.4 (4)
C5—C4—C3	115.8 (4)	C29—C28—C27	114.2 (4)
C5—C4—H4A	108.3	C29—C28—H28A	108.7
C3—C4—H4A	108.3	C27—C28—H28A	108.7
C5—C4—H4B	108.3	C29—C28—H28B	108.7
C3—C4—H4B	108.3	C27—C28—H28B	108.7
H4A—C4—H4B	107.4	H28A—C28—H28B	107.6
O1—C5—C6	121.2 (4)	O5—C29—C30	121.6 (5)
O1—C5—C4	121.1 (4)	O5—C29—C28	120.7 (5)
C6—C5—C4	117.6 (4)	C30—C29—C28	117.6 (4)
C1—C6—C5	119.3 (4)	C25—C30—C29	120.0 (4)
C1—C6—C7	121.4 (4)	C25—C30—C31	121.7 (4)
C5—C6—C7	119.3 (4)	C29—C30—C31	118.2 (4)
C6—C7—C8	109.5 (3)	C30—C31—C32	109.3 (3)
C6—C7—C14	111.6 (4)	C30—C31—C38	112.1 (3)
C8—C7—C14	112.3 (4)	C32—C31—C38	110.9 (4)
C6—C7—H7	107.7	C30—C31—H31	108.2
C8—C7—H7	107.7	C32—C31—H31	108.2
C14—C7—H7	107.7	C38—C31—H31	108.2
C13—C8—C9	120.0 (4)	C37—C32—C33	119.5 (4)
C13—C8—C7	121.4 (4)	C37—C32—C31	121.9 (4)
C9—C8—C7	118.6 (4)	C33—C32—C31	118.6 (4)
O2—C9—C8	121.1 (5)	O6—C33—C32	121.0 (4)
O2—C9—C10	121.2 (5)	O6—C33—C34	120.6 (4)
C8—C9—C10	117.7 (4)	C32—C33—C34	118.3 (4)
C9—C10—C11	113.9 (4)	C33—C34—C35	114.0 (4)
C9—C10—H10A	108.8	C33—C34—H34A	108.7
C11—C10—H10A	108.8	C35—C34—H34A	108.8
C9—C10—H10B	108.8	C33—C34—H34B	108.7
C11—C10—H10B	108.8	C35—C34—H34B	108.7
H10A—C10—H10B	107.7	H34A—C34—H34B	107.6
C10—C11—C24	109.2 (4)	C34—C35—C48	110.4 (4)
C10—C11—C12	108.1 (3)	C34—C35—C36	108.3 (4)
C24—C11—C12	111.3 (4)	C48—C35—C36	111.1 (4)
C10—C11—C23	109.6 (4)	C34—C35—C47	110.7 (4)
C24—C11—C23	109.7 (4)	C48—C35—C47	108.1 (4)
C12—C11—C23	108.9 (4)	C36—C35—C47	108.3 (4)
C13—C12—C11	112.8 (3)	C37—C36—C35	112.4 (4)
C13—C12—H12A	109.0	C37—C36—H36A	109.1
C11—C12—H12A	109.0	C35—C36—H36A	109.1
C13—C12—H12B	109.0	C37—C36—H36B	109.1
C11—C12—H12B	109.0	C35—C36—H36B	109.1
H12A—C12—H12B	107.8	H36A—C36—H36B	107.9
C8—C13—N1	120.6 (4)	C32—C37—N2	120.1 (4)
C8—C13—C12	124.2 (4)	C32—C37—C36	124.2 (4)
N1—C13—C12	115.2 (4)	N2—C37—C36	115.6 (4)
C19—C14—C15	119.6 (5)	C43—C38—C39	119.5 (5)
C19—C14—C7	121.1 (4)	C43—C38—C31	119.9 (4)
C15—C14—C7	119.3 (4)	C39—C38—C31	120.6 (4)
C16—C15—C14	120.9 (5)	C38—C39—C40	121.6 (5)
C16—C15—H15	119.6	C38—C39—H39	119.2
C14—C15—H15	119.6	C40—C39—H39	119.2
C17—C16—C15	117.5 (5)	C41—C40—C39	117.7 (6)
C17—C16—H16	121.3	C41—C40—H40	121.1
C15—C16—H16	121.3	C39—C40—H40	121.1
C18—C17—C16	122.0 (6)	C40—C41—C42	121.5 (6)
C18—C17—O3	110.6 (5)	C40—C41—O7	128.0 (6)
C16—C17—O3	127.4 (6)	C42—C41—O7	110.4 (5)
C17—C18—O4	110.6 (5)	C41—C42—O8	110.3 (5)
C17—C18—C19	122.6 (5)	C41—C42—C43	121.8 (5)
O4—C18—C19	126.8 (5)	O8—C42—C43	127.9 (5)
C18—C19—C14	117.4 (5)	C42—C43—C38	117.8 (5)
C18—C19—H19	121.3	C42—C43—H43	121.1
C14—C19—H19	121.3	C38—C43—H43	121.1
O3—C20—O4	109.8 (5)	O8—C44—O7	108.4 (5)
O3—C20—H20A	109.7	O8—C44—H44A	110.0
O4—C20—H20A	109.7	O7—C44—H44A	110.0
O3—C20—H20B	109.7	O8—C44—H44B	110.0
O4—C20—H20B	109.7	O7—C44—H44B	110.0
H20A—C20—H20B	108.2	H44A—C44—H44B	108.4
C3—C21—H21A	109.5	C27—C45—H45A	109.5
C3—C21—H21B	109.5	C27—C45—H45B	109.5
H21A—C21—H21B	109.5	H45A—C45—H45B	109.5
C3—C21—H21C	109.5	C27—C45—H45C	109.5
H21A—C21—H21C	109.5	H45A—C45—H45C	109.5
H21B—C21—H21C	109.5	H45B—C45—H45C	109.5
C3—C22—H22A	109.5	C27—C46—H46A	109.5
C3—C22—H22B	109.5	C27—C46—H46B	109.5
H22A—C22—H22B	109.5	H46A—C46—H46B	109.5
C3—C22—H22C	109.5	C27—C46—H46C	109.5
H22A—C22—H22C	109.5	H46A—C46—H46C	109.5
H22B—C22—H22C	109.5	H46B—C46—H46C	109.5
C11—C23—H23A	109.5	C35—C47—H47A	109.5
C11—C23—H23B	109.5	C35—C47—H47B	109.5
H23A—C23—H23B	109.5	H47A—C47—H47B	109.5
C11—C23—H23C	109.5	C35—C47—H47C	109.5
H23A—C23—H23C	109.5	H47A—C47—H47C	109.5
H23B—C23—H23C	109.5	H47B—C47—H47C	109.5
C11—C24—H24A	109.5	C35—C48—H48A	109.5
C11—C24—H24B	109.5	C35—C48—H48B	109.5
H24A—C24—H24B	109.5	H48A—C48—H48B	109.5
C11—C24—H24C	109.5	C35—C48—H48C	109.5
H24A—C24—H24C	109.5	H48A—C48—H48C	109.5
H24B—C24—H24C	109.5	H48B—C48—H48C	109.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2^i	0.86	2.06	2.868 (4)	157
N2—H2···O5^ii	0.86	2.08	2.847 (4)	148

Symmetry codes: (i) x+1/2, −y+1, z; (ii) x+1/2, −y+2, z.